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32 Pine Road, Syosset
$3,545,000
5 Beds ⋅ 6 Baths ⋅ 1025444 MLS
Luxury living exactly where you want to be! Set on a private acre in one of North Syosset's most desirable tree-lined neighborhoods, this picture perfect new construction features sun drenched spaces, timeless architecture and today's most sought-after luxury amenities. A dramatic two-story foyer creates a stunning first impression, while the custom stone and shake exterior delivers exceptional curb appeal. Inside sun-filled spaces, soaring ceilings, wide-plank White Oak floors, custom millwork, and designer finishes showcase impeccable craftsmanship throughout. The heart of the home is a banquet-sized chef's kitchen featuring premium appliances, spacious walk-in pantry and seamless flow into the spectacular great room with a modern linear gas fireplace flanked by floating built-ins. Designed for both entertaining and everyday living, the thoughtfully crafted floor plan offers five en-suite bedrooms all with walk-in closets, including a first-floor guest suite with private terrace access. The luxurious primary retreat features a spa-inspired bath with two premium custom walk-in closets. Step outside to your private resort-style backyard, complete with an infinity terrace, heated salt water pool with spa, sun shelf, and automatic retractable cover. Additional highlights include designer bathrooms, large mudroom, three-car garage, and a 10-foot basement provides endless possibilities for customization. Located in the award-winning Syosset School District and just minutes from golf clubs, fine dining, shopping, and transportation, this exceptional residence offers the ultimate blend of luxury, comfort, and convenience! (virtually staged)

32 Pine Road, Syosset
211 Berry Hill Road, Syosset
$1,350,000
4 Beds ⋅ 2 Baths ⋅ 1028701 MLS
What’s Special? A truly one-of-a-kind Syosset home where history, craftsmanship and modern living come together. Step into the character and warmth of a home unlike anything else in the area. Set on a beautiful .33-acre property, this spacious 4-bedroom, 2-bath Colonial offers approximately 3,000+ square feet of living space, with distinctive architectural details and thoughtful updates throughout. Inside, you’ll find wide-plank wood floors, exposed beams, custom millwork, beautiful moldings and multiple fireplaces—details that give the home an unmistakable sense of history and craftsmanship. The updated kitchen and baths provide modern convenience while preserving the personality of the house. Outside, the property becomes even more exceptional. A large detached garage with extraordinary capacity provides tremendous flexibility for cars, a workshop, hobbies, storage or a home-based creative space. There is also a finished room within the garage area, offering additional possibilities that are difficult to find in Syosset. Recent improvements include newer HVAC and central air, new roofs, updated kitchen and baths, fresh interior paint and extensive new hardscaping and walkways. The grounds also feature an 18-foot round pool half in-ground, creating a private setting for summer entertaining and relaxation. Located in the Syosset School District, this is a property for buyers who appreciate something more than a typical house—a home with space, character, craftsmanship, history and possibilities. Some homes are simply houses. 211 Berry Hill Road is an experience!

211 Berry Hill Road, Syosset
31 Underhill Avenue, Syosset
$1,988,000
5 Beds ⋅ 4 Baths ⋅ 1025506 MLS
New luxury construction in Syosset. Experience exceptional craftsmanship and modern luxury in this stunning new construction home, thoughtfully designed with today’s lifestyle in mind. Offering five spacious bedrooms and four full bathrooms. This home seamlessly blends elegant finishes with functional living space. The main level features a desirable first floor bedroom and full bath, ideal for guests, extended family, or private home office. The heart of the home is a chef inspired gourmet kitchen beautifully appointed with top-of-the-line appliances, custom cabinetry, designer lighting and an open layout perfect for entertaining. The sun filled living and dining area flow effortlessly together with convenient access to the attached garage Upstairs retreat to the luxurious primary suite featuring a spacious walk-in closet and a spa like bath, complete with a soaking tub, oversized walk-in shower and premium finishes. A junior en-suite offers its own private full bath with a walk-in shower while two additional generously sized bedrooms share a beautiful appointed full bath. A conveniently located second floor laundry room completes the upper level. Every detail has been carefully selected from the designer lighting and elegant fixtures to the high-quality craftsmanship found throughout. Simply unpack, add your personal style and enjoy effortless luxury. Perfectly situated within the Syosset school district this exceptional home is just minutes from major highways, the Syosset library, parks, shopping, dining and everything the community has to offer. A rare opportunity to own a brand new luxury home in one of Long Island’s most sought after neighborhoods. This is truly one you don’t want to miss!

31 Underhill Avenue, Syosset
175 The Vale, Syosset
$830,000
3 Beds ⋅ 3 Baths ⋅ 1025118 MLS
Most sought after gated condo in the Syosset area with owners suite on main floor. This 3 bedroom 3 bath sundrencehd home enhanced with generous high ceilings and skylights is a truly remarkable residence. Stone fireplace, huge deck and walk out lower level with a second deck that leads to a lush green private park like setting. Enjoy country club living in your own back yard. Hidden Ridge is a gated community that offers lighted tennis courts, basketball, playground, club house, heated pool and much more. Approx 1/8 mile to railroad station with plenty of shopping and restaurants to enjoy. Best complex, best location more than the mind can ever imagine ensuring you fee right at home from day one. You get a harmonious blend of tranquility and sophistication with an open floor plan. Don't miss this once in a lifetime opportunity to reside in Hidden Ridge resort style living. Syosset schools

175 The Vale, Syosset
216 Woodbury Road, Woodbury
$899,900
4 Beds ⋅ 3 Baths ⋅ 1020349 MLS
Come and See this Oversized Colonial with 4 beds and 2.5 bath located in Syosset school district. Plenty of room for extended family. Close to shopping, transportation and major roadways.

216 Woodbury Road, Woodbury
10 Clemson Lane, Woodbury
$1,525,000
5 Beds ⋅ 4 Baths ⋅ 1025222 MLS
Expanded Splanch with Endless Possibilities in the Syosset School District! Offering approximately 3,170 square feet of versatile living space on .21 acres, this beautifully expanded Splanch is designed to accommodate today's evolving lifestyles. Featuring 5 spacious bedrooms and 3.5 baths, this exceptional home offers the flexibility of two primary bedroom suites—ideal for multi-generational living, extended guests, or the potential for rental income with proper permits. The heart of the home is the brand-new kitchen, thoughtfully updated with new cabinetry, countertops, backsplash, oven, dishwasher, microwave drawer, and cooktop exhaust, creating a stylish and functional space for everyday living and entertaining. A first-floor bedroom or home office adds even more versatility to the floor plan, while the finished basement provides valuable additional living space perfect for a recreation room, media room, gym, or play area. Completing the home is a 2-car garage with electric charger offering ample storage and convenience. Located in the Syosset School District, this exceptional home combines space, flexibility, and modern updates. Whether you're looking for room to grow, space for extended family, or a home with income potential, this property offers endless possibilities to fit your lifestyle.

10 Clemson Lane, Woodbury
41 Cambria Road, Syosset
$950,000
4 Beds ⋅ 3 Baths ⋅ 1020752 MLS
Expanded Ranch in the heart of Clearview Village, located in the award-winning Syosset School District! Only a few blocks to supermarkets, shopping, Syosset Library, and local transportation. This spacious mid-block home offers numerous updates and a desirable layout for today's lifestyle. The oversized updated eat-in kitchen is the heart of the home, perfect for everyday living and entertaining. Enjoy the convenience of ALL GAS utilities, including gas heat and cooking, plus first-floor laundry, and all hardwood floors. The main level features three bedrooms and two full baths, while the second floor offers a spacious fourth bedroom with a private office, and an additional full bath—ideal for guests, or a work-from-home setup. The full finished basement provides exceptional bonus living space, perfect for a playroom, recreation room, home theater, or entertaining. An oversized backyard offers plenty of room for outdoor enjoyment, and a detached two-car garage completes this exceptional property. Conveniently located near parks, shopping, dining, supermarkets and major transportation. Move right in and enjoy all that Syosset has to offer!

41 Cambria Road, Syosset
15 Tiber Road, Oyster Bay Cove
$2,575,000
5 Beds ⋅ 4 Baths ⋅ 1022670 MLS
Freshly Painted & Re-Done Basement - Welcome to 15 Tiber Road, located on a beautiful 2-acre property in Oyster Bay Estates and within the Syosset School District. This sprawling warm and inviting ranch offers exceptional space and functionality with generous room sizes and a thoughtful layout ideal for today’s lifestyle. The primary suite features an ensuite bath and closets, creating a private retreat within the home. 3 additional large bedrooms and a full bath. On the opposite side of the home is a separate office/bedroom with a full bath that provides the perfect setup for guests, extended family, or a private work-from-home space. The expansive walk-out basement spans the full length of the home, offering endless possibilities for recreation, entertaining, gym space, or additional living quarters. Step outside to an incredible property designed for entertaining and relaxation. Enjoy summers by the heated inground gunite pool, unwind by the fire pit, or host gatherings with ease thanks to the cabana and sports court. The beautifully designed outdoor space offers privacy and resort-style living right in your own backyard. A rare opportunity to own a true ranch retreat.

15 Tiber Road, Oyster Bay Cove
39 Cherry Lane, Syosset
$2,688,000
5 Beds ⋅ 6 Baths ⋅ 1020663 MLS
Discover the perfect blend of comfort, style, and functionality in this exceptional expanded Ranch, where a charming front porch welcomes you home and sets the stage for the warm, inviting living spaces within, all located in the Syosset School District. Thoughtfully designed with spacious sun-filled interiors, soaring ceilings, skylights, and dramatic walls of windows. An open layout connecting the dining and living room spaces features an impressive cathedral ceiling, exposed wood beam accents, custom built-ins and expansive windows. Filled with natural light and timeless architectural details, this inviting space is perfect for everyday living and entertaining. The gourmet eat-in kitchen is the heart of the home, featuring premium appliances, granite countertops, a generous center island, and abundant workspace for gathering with family and friends. The luxurious first-floor primary suite provides a private retreat with a cozy fireplace, spa-inspired bath, oversized room size closet, home office, and direct access to the backyard deck. Three additional bedrooms and two full baths complete the main level, while a private, spacious second-floor guest suite/playroom with its own bath offers the perfect space for extended family or visitors. The finished lower level expands the living space with a media room featuring a fireplace, fitness area, full bath, and outside entrance, creating endless possibilities for work, recreation, or multi-generational living. Designed for year-round comfort, this home also includes radiant heat, a whole-house generator, and a heated two-car garage with epoxy flooring. Step outside to your own backyard retreat with an expansive deck overlooking the heated inground gunite pool, surrounded by mature landscaping that provides beauty and privacy. Offering an incredible combination of space, quality, and amenities in one of Long Island’s most sought-after communities, this is an exceptional opportunity to own a truly special home just minutes from shopping, parks, transportation, and everything Syosset has to offer.

39 Cherry Lane, Syosset
192 Burtis Lane, Muttontown
$3,995,000
5 Beds ⋅ 6 Baths ⋅ 1018900 MLS
There are homes that simply offer space, and there are homes that define a lifestyle. Perfectly positioned on almost two secluded acres within the Incorporated Village of Muttontown and served by the highly acclaimed Syosset School District, this exceptional Hamptons-inspired estate represents a rare opportunity to enjoy timeless architecture, modern technology, and effortless luxury in one of Long Island's most prestigious settings. Encompassing approximately 7,000 square feet, this five-bedroom, five-and-a-half-bath residence has been comprehensively reimagined from top to bottom. Every major component—from the electrical and mechanical systems to the roof, windows, and finishes—has been thoughtfully updated, creating a home that offers the confidence of new construction while preserving the warmth, character and durability that is lacking in todays new builds. Designed with today's lifestyle in mind, the interiors are equally suited for intimate evenings or grand-scale entertaining. Sunlit living spaces flow seamlessly from one room to the next, anchored by four fireplaces that add warmth and sophistication throughout. At the heart of the home is a showpiece chef's kitchen, crafted to inspire everyone from the accomplished home cook to the most discerning culinary enthusiast. A recent expansion rivals the finest of private clubs, featuring a state-of-the-art home theater with a custom bar, a dedicated fitness studio, and flexible recreation space designed for every generation. Outside, resort-style living unfolds across meticulously landscaped grounds. The heated saltwater pool with an expansive sun shelf invites relaxed afternoons, while the pavilion, outdoor kitchen, and multiple entertaining areas create the perfect setting for everything from summer gatherings to elegant evening celebrations. Integrated smart-home technology places lighting, climate, and audio, at your fingertips, delivering a level of convenience that complements today's connected lifestyle. For collectors and automotive enthusiasts, the heated four-car garage features soaring ceilings designed to accommodate vehicle lifts, offering exceptional flexibility for additional cars or a hobby space. Whether you're seeking room to grow, looking for a peaceful retreat with an easy commute to Manhattan, or searching for an elegant home where holidays become traditions and every visit feels like a destination, this remarkable estate offers the rare combination of privacy, sophistication, and enduring value. This is more than a residence—it's the home everyone will want to come back to.

192 Burtis Lane, Muttontown
5 Buckingham Court, Muttontown
$3,550,000
4 Beds ⋅ 5 Baths ⋅ 1016622 MLS
Experience refined luxury in the exclusive gated community of Stone Hill, where exceptional craftsmanship, resort-style amenities, and carefree living come together in one of Muttontown's most sought-after private enclaves. Set on over ¾ of an acre, this beautifully designed 5,000-square-foot residence offers 4 bedrooms+, 4.5 baths, and an impeccable blend of timeless elegance and modern comfort. A dramatic double-height foyer opens to a breathtaking great room with soaring ceilings, a wall of floor-to-ceiling windows, custom millwork, built-ins, and a striking double-sided stone gas fireplace. The chef's kitchen is beautifully appointed with premium appliances, custom cabinetry, an oversized center island, separate pantry, and architectural detailing, while the elegant dining room with a coffered ceiling is ideal for entertaining. The main-level primary suite offers a luxurious retreat with a spa-inspired bath featuring a Jacuzzi, sauna, double-sided gas fireplace, and oversized closet. Two additional bedrooms complete the first floor, while the second level offers a fourth bedroom and spacious bonus room. The expansive finished lower level with 10-foot ceilings and outside entrance provides abundant space for recreation, fitness, or entertaining. Outside, the private backyard offers ample room for a pool and the ultimate outdoor retreat. Additional highlights include radiant heated floors throughout, wide-plank hardwood floors, whole-house generator, whole-house water filtration system, central vacuum, and fine custom finishes throughout. Residents enjoy 24-hour gated security, a full-service clubhouse with an indoor pool, fitness center, tennis courts, and social room, along with lawn care and snow removal through the HOA. Located in the award-winning Syosset School District, this home offers an unparalleled lifestyle in one of Long Island's premier private communities.

5 Buckingham Court, Muttontown
23 Garden Circle, Syosset
$1,990,000
5 Beds ⋅ 4 Baths ⋅ 1016366 MLS
NEW CONSTRUCTION A Stunning Residence Designed with Comfort and Functionality in Mind, Quality Craftsmanship and Finishes Reflects throughout this Five Bedroom Colonial. Offering Custom Millwork, Coffered Ceilings, 9' Ceilings, Tray Ceilings. Entry Foyer leading to Living Room & Dining Rm -Open Concept .An Expansive Open Kitchen & Family Room overlooking private backyard provides a Relaxing Atmosphere. The Thoughtfully Designed Primary Suite Combines Comfort, Elegance - Generous Space Includes Two Walk-in Closets, Bright Spa-Inspired Bathroom with a Soaking Tub, Custom Vanities. A Convenient 1st Fl Bedroom Suite provides much Flexibility & Versatile Space-such as Office Option , Playroom ,Fitness Room and Adds Long Term Value to this Well Built Home. Outside Entrance to Basement Provides for more Space and Flexibility. Please Note ALL UTILITIES Connections are INCLUDED. Seller will Listen to all Reasonable Offers. Close Convenience to All -Shops, Schools, Dining and Transportation

23 Garden Circle, Syosset
5 Westgate Road, Muttontown
$3,680,000
5 Beds ⋅ 6 Baths ⋅ 1016748 MLS
Top Syosset School District, Don't miss this wonderful better than new 5-bedroom home located in the gated community of Stone Hill Muttontown. Nestled within an exclusive private HOA community, zoned for pool,24 hour security, club house, indoor pool, tennis, lawn and snow removal. this luxurious estate provides the perfect blend of privacy, and modern comfort. Set on a sprawling 1.33 acre lot of elevated terrain, the home commands a stately presence with over 6661 square feet of refined living space. Upon entering, guests are greeted by soaring high ceilings that enhance the sense of openness and light throughout the home. Architectural details such as custom millwork, and expansive windows add sophistication and warmth to each room. The residence features 5 spacious bedrooms and 5.5 elegantly appointed bathrooms, each designed with high-end finishes, natural stone, and designer fixtures. The primary suite is a sanctuary of its own, complete with a sitting area, spa-inspired en-suite bath, and oversized walk-in closets. Living spaces are ideal for both entertaining and everyday luxury, including formal and casual living and dining areas, a chef’s kitchen with top-tier appliances and custom cabinetry, and a private home office. Outdoor living is just as impressive: lush landscaping surrounds the property, providing both beauty and seclusion. The elevated setting offers serene views and excellent drainage. There's ample space for a fish pond, outdoor kitchen, and garden retreats—perfect for enjoying the temperate climate in complete privacy. Backyard with BBQ area.

5 Westgate Road, Muttontown
36 Richmond Street, Syosset
$998,888
5 Beds ⋅ 2 Baths ⋅ 1012561 MLS
Welcome to this beautifully maintained sprawling ranch offering over 1,600 square feet of comfortable living space, perfectly blending charm, functionality, and convenience. Step inside to discover a warm and inviting open floor plan enhanced by hardwood floors and abundant natural light. The heart of the home is the fully renovated eat-in kitchen, featuring a spacious center island, ample cabinetry, and modern finishes—ideal for both everyday living and entertaining. Adjacent to the kitchen are the formal dining area and generous living room, creating a seamless flow throughout the main living spaces. This home offers four generously sized bedrooms, each providing comfort and ample closet space. In addition, the converted garage serves as a versatile bonus room or fifth bedroom, perfect for guests, a home office, gym, or playroom. Recent improvements include a brand-new driveway, adding both curb appeal and convenience. With its energy-efficient features, utility costs remain remarkably low, making homeownership even more affordable! Located within the highly acclaimed Syosset School District and benefiting from exceptionally low taxes, this property offering the perfect combination of comfort, style, and practicality, walking distance to shopping, dinning, LIRR and much more!

36 Richmond Street, Syosset
2 Greenwood Lane, Woodbury
$2,299,999
5 Beds ⋅ 5 Baths ⋅ 1015209 MLS
Welcome to 2 Greenwood Lane! A Massive Contemporary Estate situated on a premier, park-like acre within the prestigious Rolling Hills area of Syosset School District. This expansive 5-bedroom, 4.5-bathroom home offers an unparalleled combination of grand scale, structural integrity, and architectural warmth. From the moment you step into the soaring two-story center hall foyer, you are greeted by an inviting, open-concept layout that allows you to see the true expanse of the home. Designed for both grand entertaining and comfortable daily living, the main level features a sun-drenched formal living room, a gracious formal dining room, and a massive den off the kitchen complete with a custom bar—perfect for hosting gatherings. Upstairs, the sleeping quarters are remarkably spacious, highlighted by a sprawling primary suite featuring dual walk-in closets and a dedicated en-suite bath. A massive, full finished basement with high ceilings offers the perfect footprint for a home theater, gym, or recreation area. Step outside onto a trex deck and overlook your own private paradise. The meticulously landscaped, park-like yard features a sweeping patio surrounding a pristine in-ground pool—your private summer country club. This home has been meticulously maintained, it is the perfect opportunity to bring your own personal style and vision to a beautifully maintained estate. This is your chance to create a forever home of your own in one of Woodbury's most desirable neighborhoods. 3D Tour: https://my.matterport.com/show/?m=WmMqijM6QPP

2 Greenwood Lane, Woodbury
7 Walters Avenue, Syosset
$949,999
4 Beds ⋅ 2 Baths ⋅ 1012570 MLS
Super low taxes with walking distance to LIRR in Syosset! This spacious 4-bedroom, 2-full-bathroom charming home featuring high ceilings on every level, creating a bright and airy atmosphere throughout. The kitchen and bathrooms have been tastefully updated within the last five years, offering modern finishes and move-in-ready convenience. The full unfinished basement provides tremendous potential for additional living space, a recreation room, home office, gym, or abundant storage. Situated on an oversized 10,000+ sqft lot, this property offers exceptional opportunities for expansion, renovation, or new construction. Conveniently located near shopping, dining, parks, and transportation. A rare opportunity to own a versatile property with endless possibilities in a highly desirable location with Syosset SD!

7 Walters Avenue, Syosset
37 Church Street, Syosset
$1,575,000
6 Beds ⋅ 5 Baths ⋅ 1012793 MLS
EXCEPTIONAL NEW VALUE IN NEW CONSTRUCTION! Understanding the challenges of today’s higher interest rate environment and evolving real estate market, the builder has proactively adjusted pricing to create an exceptional opportunity for today’s homebuyers. Experience the same uncompromising quality, thoughtful design, luxurious finishes, and fine craftsmanship of brand-new construction at a more attractive price point. An outstanding opportunity to own a beautiful new home where exceptional quality meets exceptional value! 5 Bedroom, 6 Bath, Colonial, Bright Open Floor Plan, Gourmet Eat In Kitchen, Hardwood Floors, CAC, Master Suite w/Walk in Closet, Family Room w/ Fireplace. Stunning Appointments And Eye Catching Millwork! Conveniently located in the Heart of North Syosset. Close to Shops, Restaurants, & Railroad. Completely Built

37 Church Street, Syosset
5 Kodiak Drive, Woodbury
$4,450,000
8 Beds ⋅ 9 Baths ⋅ 000011 MLS
Introducing the most sought-after home in Woodbury, 5 Kodiak Drive. An epitome of contemporary luxury nestled in Syosset School District. This architectural masterpiece redefines opulence with its sleek design and an array of innovative amenities, ensuring a lifestyle of unparalleled comfort and sophistication. Situated on a sprawling one-acre lot, this estate seamlessly combines modernity with timeless elegance. As you step through the grand entrance, you're greeted by a fusion of sleek lines and luxurious materials, setting the stage for an exceptional living experience. Crafted for the most discerning homeowner, this residence boasts 8 bedrooms and 9 bathrooms, each meticulously designed with premium finishes and thoughtful details. Smart climate control systems, integrated sound, and lighting elevate the living experience to new heights. The main level is a haven for relaxation and entertainment. A stylish bar room invites you to unwind by the fireplace, while the formal dining room offers the perfect setting for intimate gatherings. The gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, pizza oven, custom cabinetry, and a breakfast area overlooking the lush backyard. Outside, the expansive grounds offer a sanctuary for outdoor living. A private tennis court with overhead lighting provides endless opportunities for recreation, while the heated in-ground Gunite pool and cabana area offer a serene retreat for lazy afternoons and al fresco dining. The pool features an infinity edge and a mesmerizing water feature with multiple fire elements, creating a captivating ambiance. Upstairs, the primary suite is a luxurious escape, complete with a sitting area, private balcony, and spa-like ensuite bath featuring a soaking tub and steam shower. Four additional bedrooms, each with its own ensuite bathroom, provide ample space for family and guests. Downstairs, the lower level is a hub of activity, with a fitness room, billiards area, and home theater offering endless entertainment options. A three-car garage provides ample space for vehicles and storage, while smart home features ensure convenience and security. With its blend of contemporary design and timeless elegance, this estate sets a new standard for luxury living in Woodbury, NY, offering a lifestyle characterized by indulgence, sophistication, and unparalleled amenities.

5 Kodiak Drive, Woodbury
249 Cold Spring Road, Syosset
$1,848,000
5 Beds ⋅ 4 Baths ⋅ 1006505 MLS
Enjoy suburban calmness with city accessibility in the top-rated Syosset School District. Commuting is effortless with the Syosset LIRR station just minutes away, providing under 55-minute express service to Penn Station and Grand Central Madison. This secure, quiet home features a full ADT security system and underwent comprehensive renovations in 2018, including new infrastructure (roof, siding, windows, electric, and plumbing). The property offers five bedrooms, four bathrooms, and a light-filled kitchen with cozy radiant heat flooring. Expansive front and back decks perfect for outdoor family entertaining. Offering the perfect blend of lower taxes and unparalleled convenience, this home has it all. With expansive land available, you can extend your property to your desired size and enjoy endless possibilities for outdoor activities. Must see!!

249 Cold Spring Road, Syosset
23 Woodbury Road, Woodbury
$2,999,000
5 Beds ⋅ 6 Baths ⋅ 1005913 MLS
Welcome to Crest Hill! An extraordinary luxury estate set on 2.02 private acres in the heart of prestigious Woodbury, New York. Offered fully furnished and completely turnkey, this remarkable residence combines timeless elegance with modern sophistication for an unparalleled North Shore lifestyle. A grand mansion-style approach welcomes you home with an expansive front driveway framed by stately brick piers, already wired and prepared for iron security gates controlled directly from within the residence. Every detail has been thoughtfully designed to create a private sanctuary of luxury, comfort, and distinction. This magnificent 10-room Colonial offers 5 spacious bedrooms and 6 designer bathrooms, all flooded with natural sunlight through oversized windows and soaring architectural spaces. The dramatic sunlit entry foyer introduces the home with exquisite porcelain flooring and an impressive custom curved bridal staircase adorned with wrought iron and brass detailing. Designed for both elegant entertaining and everyday living, the open-concept layout seamlessly connects the gourmet kitchen to the grand great room featuring an elegant gas fireplace. The flow continues beautifully into the formal living room with a second gas fireplace toward the stunning double mahogany and glass entry doors that create a striking architectural statement. A first-floor guest or in-law suite provides ideal accommodations for extended family or visitors. Upstairs, the luxurious primary suite and second bedroom suite each feature private Juliet balconies overlooking the serene courtyard and surrounding natural landscape. Spa inspired designer baths throughout the home include premium finishes, with the principal bath featuring heated flooring for ultimate comfort. The fully finished lower level expands the home’s exceptional living space and includes a gym, two legal egresses, a media room wired and ready for a custom home theater, and endless possibilities for recreation, wellness, or private retreat spaces. Exterior features an outdoor kitchen with gas BBQ, sink, beverage cooler, storage and more. The double width driveway from top to bottom allows for passing another car and additional parking for parties. An extensive entertainment patio off the kitchen lends itself to another world of outdoor living. Permits are in place for an inground pool and lighting, approved by the town. The architecture of the home is complemented by concrete walls, special pathways, and a garden walk on the hillside. Crest Hill is truly an entertainer’s dream; a residence where luxury, privacy, and functionality exist in perfect harmony. Simply bring your designer bags and step into your own private world of sophistication. Ideally situated near the Long Island Rail Road, the Villages of Huntington and Cold Spring Harbor, and the renowned Woodbury shopping district, the location offers convenient access to elegant dining, boutique shopping, hiking trails, boating, fishing, and the very best of Long Island’s celebrated North Shore lifestyle. Beautiful Long Island beaches are just 15 minutes away by car. Crest Hill is more than a home, it is a statement of luxury living. Make this dream home your next stop! View 3d tour, click virtual tour link for video and more.

23 Woodbury Road, Woodbury
119 Plainview Road, Woodbury
$1,999,999
6 Beds ⋅ 5 Baths ⋅ 1005538 MLS
Welcome to 119 Plainview Road — a place where elegance meets ease. This expansive 4,500-square-foot Colonial rests on over an acre of pondfront property in Woodbury, where every inch has been thoughtfully maintained to create a home that feels as effortless as it is impressive. Inside, six generous bedrooms and four and a half bathrooms offer space for family and guests alike, all finished with high-end appointments throughout. Every detail has been meticulously cared for, presenting in turn-key, move-in condition for the most discerning buyer. The true showpiece lies beyond the walls. Step outside to a country-club-caliber backyard where an inground pool anchors a private oasis overlooking serene pond views. Whether entertaining on a grand scale or enjoying a quiet morning by the water, the oversized lot delivers privacy and resort-style living rarely found this close to everything. Located within the prestigious Syosset School District and minutes from premier shopping, dining, and parkway access, this is a rare opportunity to own a true estate property on Long Island!

119 Plainview Road, Woodbury
1780 Route 106 Unit #C, Muttontown
$3,995,000
5 Beds ⋅ 6 Baths ⋅ 1004527 MLS
Steeped in architectural pedigree and timeless elegance, this extraordinary Muttontown estate, on 3.84 bucolic acres, was designed by renowned architect Marion Sims Wyeth. Privately tucked behind an impeccably landscaped half mile-long drive off Route 106, the property unfolds as a secluded North Shore sanctuary of exceptional beauty and distinction in the acclaimed Syosset School District. Set amidst sweeping lawns, manicured gardens, and picturesque equestrian grounds, the stately brick residence, crowned with a slate roof and introduced by a charming courtyard entry, exudes enduring sophistication. Inside, grand formal entertaining rooms showcase exquisite millwork, original hardwood floors, dramatic wrought-iron railings, and an abundance of French doors that flood the interiors with natural light while seamlessly connecting the home to its breathtaking surroundings. Offering five bedrooms and five-and-a-half baths, the home masterfully balances grandeur with comfort. The formal living room, complete with a fireplace and built-in wet bar, creates an inviting setting for entertaining, while the sunlit breakfast turret and updated chef’s kitchen, appointed with premium professional-grade appliances, provide effortless everyday functionality. A spacious family room and elegant powder room complete the main living spaces. The first-floor primary suite serves as a luxurious private retreat, featuring dual full baths, a fireplace, expansive walk-in closets, and an intimate sitting room. The upper level offers two generously proportioned bedrooms and a beautifully appointed full bath with a thoughtfully separated vanity and shower area. Completing the space is an expansive unfinished attic, presenting exceptional potential for storage or future customization. Additional highlights include a walk-out finished lower level with laundry, bedroom with full bathroom and direct access to the attached two-car garage. Designed for both gracious living and sophisticated entertaining, the residence boasts expansive slate terraces spanning the length of the home, overlooking the stone courtyard driveway, private gardens, charming pergola, and in-ground gunite pool - evoking the romance and refinement of a storybook North Shore estate. A true horse property, the fully fenced equestrian amenities are equally exceptional, featuring a pristine multi-stall barn built-by Morton, thoughtfully designed grazing paddocks, and scenic walking trails woven throughout the grounds. A truly rare offering, this remarkable estate presents an unparalleled opportunity to own a significant piece of Long Island history.

1780 Route 106 Unit #C, Muttontown
55 Coves Run, Oyster Bay Cove
$5,649,000
7 Beds ⋅ 8 Baths ⋅ 1001796 MLS
OYSTER BAY COVE. Set at the end of a serene cul-de-sac, this 9,400 sq. ft. estate blends modern luxury with European-inspired elegance on magnificent resort-style grounds offering exceptional privacy. A grand circular cobblestone driveway with fountain sets the tone for this impressive residence featuring soaring ceilings, sun-drenched interiors, expansive windows, and a dramatic open layout designed for both grand entertaining and comfortable living. The home offers 7 bedrooms and 7.5 baths with exquisite architectural details throughout. The chef’s kitchen features top-of-the-line appliances, custom cabinetry, and an oversized island. Elegant living spaces include a formal dining room, grand living room, billiard room, and private home office. The lower level is a true retreat with a basketball court, home theater, full bar, lounge, and wet & dry saunas. Outdoors, enjoy a heated gunite pool, spa, private tennis court, multiple balconies, and beautifully manicured grounds with multiple entertaining areas. A rare offering complete with a three-car garage, delivering resort-style living and unmatched privacy in a one-of-a-kind luxury estate.

55 Coves Run, Oyster Bay Cove
76 Wyoming Court, Syosset
$1,698,888
5 Beds ⋅ 4 Baths ⋅ 1001913 MLS
Brand New Completed Construction! Step into luxury with this brand new Center Hall Colonial, nestled in a center block location. Crafted by a builder renowned for his impeccable design and craftsmanship, this home is a gem in the making. From the moment you walk through the grand two-story entryway, you’ll be swept away by the elegance and attention to detail. The home features 5 spacious bedrooms, 4 full bathrooms, and gleaming hardwood floors throughout. The state-of-the-art kitchen is a chef’s dream, complete with stainless steel appliances. The den/family room, with its cozy gas fireplace, is perfect for relaxing or entertaining. And let’s not forget the full basement with its own outside entrance – the possibilities are endless. The home also features stunning tray and coffered ceilings add an extra layer of sophistication and charm. Buyer is responsible for transfer tax, water/sewer and gas hookups($7,500), final survey($950), and transfer tax.

76 Wyoming Court, Syosset
15 Hillvale Road, Syosset
$1,235,000
4 Beds ⋅ 3 Baths ⋅ 1001415 MLS
Bright, spacious, and beautifully maintained located on a quiet, friendly street in one of Long Island’s most desirable neighborhoods! Approx. 7,000 sqft lot with a large outdoor deck 4 Bedrooms & 3 Bathrooms Approx. 1,796 sqft interior living space + finished basement Fully renovated with high-quality upgrades about 6 years ago Gas heating system and central air conditioning Detached 2-car garage with oversized private driveway Convenient Location: Easy access to Northern State Parkway and Long Island Expressway (I-495). Close to Woodbury Rd and Route 106 shopping, restaurants, and everyday conveniences.

15 Hillvale Road, Syosset
21 Chauncey Place, Woodbury
$2,548,000
5 Beds ⋅ 6 Baths ⋅ 993715 MLS
Welcome to this exceptional custom-built Colonial nestled in the highly sought-after Swan Lake development of Woodbury, located within the award-winning Syosset School District. Boasting approximately 6,000 square feet of thoughtfully designed living space, this magnificent residence offers 12 spacious rooms, including 5 generously sized bedrooms—each featuring its own walk-in closet—and 6 full bathrooms. Crafted with superior quality and attention to detail, this home features stunning marble and granite finishes throughout, creating a timeless and elegant atmosphere. The expansive layout offers seamless flow, ideal for both everyday living and entertaining on a grand scale. The fully finished basement with outside entrance provides versatile additional living space, perfect for recreation, guests, or extended family. Step outside to a beautifully level and private backyard, where luxury meets lifestyle. The outdoor kitchen area is a true showpiece, complete with a pizza oven imported directly from Italy—perfect for entertaining and creating unforgettable experiences. This one-of-a-kind residence is more than just a home—it’s a true oasis offering sophistication, comfort, and exceptional craftsmanship in one of Woodbury’s premier locations.

21 Chauncey Place, Woodbury
21 Kodiak Drive, Woodbury
$2,200,000
5 Beds ⋅ 5 Baths ⋅ 992528 MLS
Located within the prestigious gated community of The Gates in Woodbury, this exceptional 5 bedroom, 5 bath residence offers the perfect blend of elegance and everyday livability on a breathtaking one acre park-like setting. Designed with entertaining in mind, the home features spacious principal rooms that flow seamlessly from one to the next. The inviting den is a true showstopper, anchored by a cozy fireplace, warmed by radiant heated floors, and opening directly to the patio through walkout access, making indoor-outdoor living effortless. The primary suite is a private retreat, complete with a beautifully renovated en suite bath. Step outside and discover a lush, expansive acre with endless possibilities, ample room to add a pool or simply enjoy the serene, park-like grounds as they are. Syosset School District.

21 Kodiak Drive, Woodbury
71 Eagle Chase, Woodbury
$1,180,000
3 Beds ⋅ 3 Baths ⋅ 991676 MLS
Welcome to 71 Eagle Chase, a beautiful home in the prestigious 24-hour gated Eagle Chase community, featuring 3 bedrooms and 2.5 bathrooms. Enter through grand double doors into a bright, open-concept layout with soaring vaulted ceilings and a skylight that fills the space with natural light. The main level includes a guest bedroom with a private balcony, a home office, and a powder room. The eat-in kitchen flows seamlessly into the formal dining area and spacious living room, highlighted by a cathedral ceiling and a cozy wood-burning fireplace. Sliding doors lead to a deck patio, perfect for outdoor entertaining. Upstairs, the primary suite offers a vaulted ceiling, private balcony, two walk-in closets, and an en-suite bath with a soaking tub and separate shower. A third bedroom features two large closets, a balcony, and access to a full bath. An open landing provides space for a sitting area or reading nook, along with a conveniently located washer and dryer. Enjoy resort-style living with a newly renovated clubhouse featuring a gym, lounge, kitchen, locker rooms, pool, tennis, and pickleball. Located in the highly desirable Syosset School District. Short Sale Subject to Lenders Approval.

71 Eagle Chase, Woodbury
7 Windemere Crest, Woodbury
$2,895,000
6 Beds ⋅ 6 Baths ⋅ 989712 MLS
Welcome to this stunning, fully gut-renovated Contemporary nestled on one of the largest lots in the prestigious gated community of Windemere — a rare 1.26-acre private cul-de-sac setting with room for a pool and endless possibilities. From the moment you arrive via the elegant circular driveway, this 5-bedroom, 5.5-bath showpiece makes an unforgettable impression. Thoughtfully designed with soaring ceiling heights and an open-concept layout, walls of glass and sliders flood every room with natural light, creating a bright, airy atmosphere throughout. The designer kitchen is a true centerpiece, featuring high-end appliances and seamlessly flowing into a sun-drenched sunroom and a massive great room — perfect for everyday living and effortless entertaining. A wet bar and sleek linear fireplace add sophistication to the living spaces, while the upstairs loft offers flexible additional living space. The main-floor primary suite is a private sanctuary unto itself, complete with sliding glass doors opening to the expansive Trex deck, floating stairs, a custom walk-in closet, and a spa-inspired bath boasting radiant heat flooring, a built-in towel warmer, and a freestanding soaking tub. Step outside to your own resort-style backyard retreat — a massive Trex deck with a full outdoor kitchen and multiple lounge and dining areas, with stairs leading down to the sprawling backyard. The full finished walk-out basement adds tremendous additional living and entertaining space, completing this exceptional offering. A truly rare opportunity in one of the area's most sought-after communities.

7 Windemere Crest, Woodbury
49 Canterbury Road, Woodbury
$1,379,000
3 Beds ⋅ 3 Baths ⋅ 966567 MLS
An Exceptional Woodbury Retreat with Incredible Outdoor Living... Welcome to 49 Canterbury Road, a beautifully maintained expanded split-level home in Woodbury, NY, located within the Syosset School District and offering convenient access to Syosset, major highways, the Long Island Rail Road, shopping, dining, and nearby community parks. At the heart of the home is a beautifully updated, spacious eat-in kitchen featuring stainless steel appliances, an island, abundant cabinetry, generous prep space, and views overlooking the spectacular backyard. Sun-filled living and dining spaces flow effortlessly throughout the home, while two natural gas fireplaces bring warmth and character to the living and family rooms. The flexible floor plan features three generously sized bedrooms, two and a half bathrooms, and additional living space ideal for a home office, den, media room, playroom, or guest space. The finished lower level provides even more versatility and room to make the home your own. Step outside and discover what truly sets 49 Canterbury apart. The beautifully landscaped backyard creates an exceptional setting for outdoor living and entertaining, featuring an in-ground heated pool and generous areas for dining, gathering, relaxing, and enjoying the outdoors. Additional highlights include central air conditioning, generous storage, and a home that has been thoughtfully maintained over the years. Enjoy the updated kitchen, spacious layout, spectacular outdoor setting, and the opportunity to bring your own vision to select interior spaces over time. For buyers searching for a home in Woodbury or the Syosset School District, 49 Canterbury offers an exceptional combination of location, space, outdoor amenities, accessibility, and the opportunity to personalize a home to your own style. Experience the lifestyle, setting, and possibilities of 49 Canterbury Road—a distinctive Woodbury home with convenient access to everything the Syosset-Woodbury area has to offer.

49 Canterbury Road, Woodbury

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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